This invention relates to novel Polymeric Urethane compositions which are obtained by reacting trialkanolamines with hydroxy fatty acids to form mono, di and/or triesters, which are further reacted with diisocyantes to form polymers, which are thereafter quaternized. The resultant polymeric urethane ester quaternary compositions of the present invention exhibit the normal characteristics of existing quaternary compositions such as conditioning, prevention of static charge and softening, emolliency, lubricity, enhanced wet and dry compability, and in addition, increased adhesion to the skin and hair. Also, increased adhesion to the skin and hair occurs as a result of the presence of the urethane linkages directly attributable to the diurethane functionalities which enhance the cationic character of tenacity of the present invention in skin and hair contacting formulations.
Quaternary amine-containing compositions have long been in existence and have been used in a myriad of applications. These compositions range from derivatives of tallow such as Dimethyl Di-Hydrogenated Tallow Ammonium Chloride which has been the standard for fabric softeners and as an antistat in fabric spray applications. Quaternaries based on Benzyl Chloride, i.e., Benzylkonium Chloride have been used in conditoners for hair; but the tendency has been to shy away from the Benzene radical, which has some definite irritation and toxicological properties. Quarternaries such as Trimethyl Cetyl ammonium chloride has long been used in hair conditioners for their outstanding compability and antistatic properties. The drawback of the prior art composition is the viscosity which necessitates the addition of water and/or solvents to make the product useable by the cosmetic manufacturer.
In contrast to the art, the compositions according to the present invention bring novel unanticipated properties which can be traced to the presence of the xe2x80x9curethane linkagexe2x80x9d within the polymer. This linkage synergistically increased adhesion to hair and skin contacting formulations resulting in the use of less quaternary than those products which are available in the current marketplace, thus resulting in a significant reduction in the cost of manufacturing personal care products. In addition, the use of polyurethane allows the manufacturer a considerable degree of flexibility for formulation due to the viscosity and molecular weight of the composition, which may vary as a function of the polymeric chain size and substituents.
One aspect of the present invention relates to a polymeric urethane ester quaternary composition which is made by reacting a trialkanolamine with a hydroxy-containing fatty acid to form a mono-, di- or triester. The ester obtained is then reacted with a diisocyanate as otherwise described herein to produce a polyurethane ester containing tertiary amine groups which tertiary amine groups may be quaternized with a quaternizing agent in optional preferred embodiments according to the present invention. Methods of making and using these compositions are also contemplated by the present invention as are personal care products which include these compositions.
Preferred non-quaternized compositions according to the present invention may be represented by a chemical formula represented by Formula I: 
wherein
R1 is a C2 to C12 saturated or unsaturated, linear, branch-chained, cyclic or aromatic hydrocarbon group which is either unsubstituted or substituted with a pendant hydroxyl group, but is preferably unsubstituted;
R2 is a C1 to C24 saturated or unsaturated, linear, branch-chained, cyclic or aromatic hydrocarbon group wherein said hydrocarbon group may be a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or a substituted alkylphenyl or alkylbenzyl group; and
R3 is a C2 through C22 (preferably, C6 through C12) linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; and
n is an integer from about 2 to 5,000, preferably about 2 to 1000, more preferably about 10 to 500.
Preferred quaternized compositions according to the present invention may be represented by a chemical formula represented by formula II: 
wherein
R1 is a C2 to C12 saturated or unsaturated, linear, branch-chained, cyclic or aromatic hydrocarbon group which is either unsubstituted or substituted with a pendant hydroxyl group, but is preferably unsubstituted;
R2 is a C1 to C24 saturated or unsaturated, linear, branch-chained, cyclic or aromatic hydrocarbon group wherein said hydrocarbon group may be a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or a substituted alkylphenyl or alkylbenzyl group;
R3 is a C2 through C22 (preferably, C6 through C12) linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group;
R4 is an electron pair (unsubstituted) or a quaternizing group;
R5 is non-existent (unreacted) or is a counterion to the quaternizing group; and
n is an integer from about 2 to 5,000, preferably about 2 to 1000, more preferably about 10 to 500.
In preferred aspects of the present invention, R3 is a C10 hydrocarbon, more preferably a methyl substituted cyclohexyl or isophorone group which is obtained after reaction of isophorone diisocyanate with the trialkanolamine esters. Preferably, R2 is obtained from the reaction of a fatty acid selected from the group consisting of caproic, caprylic, capric, lauric, myristic, palmitic, stearic, arachadonic acid, linoleic, oleic, linoleic, linolenic, 2-ethylhexoic, isooctanoic, pelargonic, heptanoic, undecanoic, isolauric, isomyristic, isopalmitic, isostearic and mixtures such as those generally known in the art as coconut fatty acids, palm kernal fatty acids, soybean fatty acids, safflower fatty acids, castor oil, etc. In addition to the aforementioned acids, alpha hydroxy acids such as lactic acid, glycolic acid, invention include for example, lactic acid, glycolic acid, alpha hydroxy butyric acid, alpha hydroxy pentanoic acid, alpha hydroxy hexanoic acid, alpha hydroxy heptanoic acid, alpha hydroxy octanoic acid, alpha hydroxy nonanoic acid, alpha hydroxy decanoic acid, alpha hydroxy dodecanoic acid, among others and beta-hydroxy acids such as salicylic acid, among numerous others, as well a ricinoleic and 12-hydroxystearic cid. In more preferred aspects of the present invention, the fatty acid is selected from the group consisting of ricinoleic acid, 12-hydroxystearic acid or mixtures thereof, or representative mixtures of fatty acids obtained from sources (triglycerides) such as castor oil, coconut oil, palm kernel oil, soybean oil, safflower oil, rape seed (canola) oil, among others. Preferred alpha hydroxy acids include lactic acid and glycolic acid. Noted here is the fact that in certain transesterification reactions involving trialkanolamines and triglycerides, the trialkanol fatty ester may represent a mixture of compositions having various fatty acid group substituents.
In particularly preferred aspects of the present invention, the trialkanolamine is triethanolamine, the acid is ricinoleic acid, lactic acid or salicylic acid, or a mixture of any one or more of the aforementioned acids in combinatnion with erucic acid and/or oleic acid. Mixtures of lactic acid and erucic acid or salicylic acid and oleic acid are also preferred for use in the present invention.
The present invention relates to polymeric urethane ester quaternary compositions (xe2x80x9cpolymeric urethane ester quatsxe2x80x9d) which are produced by taking trialkanolamines and reacting the alkanol groups with fatty acids to produce amine mono-di and triester, preferably di-esters, subjecting the di-esters to chain extension polymerization with a diisocyanate and then quaternizing free tertiary amine groups to produce compositions according to the present invention. The fatty acids which are used may be linear, isomeric or aromatic in structure ranging in length from C2 to C22 carbon atoms and in addition to containing a carboxylic acid group, also contain at least one free hydroxyl group. Included within this range of fatty acids are derivatives of Castor Oil such as 12-hydroxystearic acid, ricinoleic acid as well as castor itself.
Methods of using the present compositions in personal care products and methods of making personal care products are also aspects of the present invention.
The present compositions, when formulated in personal care products, including shampoos and conditioning products, instill exceptional characteristics of surfactancy, sheen, wet-comb, dry-comb, anti-static properties and conditioning qualities to the personal care products.